


The Panty Thief

by Exaggerated_Specificity



Category: Supernatural
Genre: Anal Fingering, Barebacking, Dean in Panties, Dirty Talk, Feminization, First Time, Frottage, Laundry, M/M, Oral Sex, Panties, Panty Kink, Plot What Plot/Porn Without Plot, Rimming, Sam In Panties, Shyness, Size Difference, Teenagers, Underage Dean Winchester/Sam Winchester, Underage Sex, Virginity
Language: English
Status: Completed
Published: 2014-03-23
Updated: 2014-03-23
Packaged: 2018-01-16 17:18:58
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 6,701
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1355470
Author URL: https://archiveofourown.org/users/Exaggerated_Specificity/pseuds/Exaggerated_Specificity
Summary: <blockquote class="userstuff">
              <p>It's Sam's turn to do laundry.  Maybe this time won't turn out to be such a bad way to spend his weekend.</p><div class="center">
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    <a href="http://brotherslovershunters.tumblr.com/post/80446703496/the-panty-thief-by-exaggerated-specificity-on-ao3"></a>
    <br/>
    <img/>
    <br/>
  </p>
</div>
            </blockquote>





	The Panty Thief

**Author's Note:**

> Instead of working on my giant SPN-J2 Big Bang fic, I let this little pornbunny infect my head for like a week. I didn't mean to write almost 7K words of Teenchester Panty!Kink, I really didn't but there was this fucking picture on @boysinlace Twitter and I just couldn't help myself.

Sam hated when it was his turn to do laundry. Chores like these always made him feel like a little kid, back when he couldn’t help out with research or even fill salt rounds. It didn’t help that his 18 year old brother was kind of a slob, which meant Sam had to spend an extra ten minutes hunched over the clothing pile that had built up around Dean’s duffle bag, extracting dirty clothes from the clean-ish ones. Sam huffed his way through the task, glaring at Dean who was sitting on their bed, oblivious to Sam’s woes, focused completely on cleaning his pearl handled Colt 1911. 

Some of the clothes reeked and Sam cringed every time his hand touched some unknown, crusty substance. Sam glared at Dean from under his too-long mop of brown waves, trying to use sheer force of will to get his brother to acknowledge the awfulness of this chore. But, despite his litany of overly loud sighs and reactionary gasps, Sam remained ignored. 

When he was finally done, Sam shoved their near empty bottle of dollar store laundry detergent and his dog eared copy of ‘Catcher in the Rye’ on top of the sweat stained t-shirts and god-knows-what-caked jeans. He slung the heavy, olive drab military duffle over his shoulder giving Dean one last dirty look before unchaining the lock on the door.

“Don’t sulk, Sammy. At least Dad’s still on that hunt. You lucked out he didn’t get back before laundry day or you’d be stuck washing his skivvies too.” Dean joked, oblivious and charming, as usual. 

“I’m gonna finish up here and take a shower. When you get back we’ll go downtown for dinner or somethin’, okay?” A peace offering. 

Sam glanced back at Dean and his million dollar grin. What a fucking dork. Sam rolled his eyes and turned away just as he felt his cheeks flush. He knew pouting was pathetic but being irrationally angry at his stupid, handsome brother was nothing new. Sure, Dean did their laundry last time, but at least he could acknowledge it was a shitty way to spend the weekend. 

“Whatever.” Sam sighed and shrugged pathetically as he let the door shut behind him. 

It was late afternoon on a weekend and the EZ Wash Laundromat was bustling with people. The smell of fabric softener and cigarette smoke made the hot, moist air inside the cramped space difficult to breathe. Sam wove through the other patrons across the black and white checkerboard tile, frowning at machine after machine already full of swirling suds. He scuttled back to the bank of industrial sized washers, normally reserved for comforters and other large items. There were two open, side by side, just recently emptied. Sam quickly staked his claim, dumping out the sack of clothes. He sorted them directly into the washers in two sizeable batches, one light and one dark. These machines were much larger capacity and cost $2.50 per load, a full dollar more than the regular washers, but this way there was no waint and fewer loads overall. He popped in the quarters, not caring that he was spending his snack budget. It would save time and that’s what mattered. 

After adding the soap and starting the wash cycle on both machines, Sam bought a can of Sprite and plopped down on one of the avocado green lobby chairs. He pulled his book out of his back pocket where he’d stashed it and flipped to the page that was folded over to hold his place. It was Sam’s fifth or sixth time through ‘Catcher.’ It had been assigned as summer reading in a school he’d never return to a few towns back. Something in it spoke to him, he couldn’t stop reading it. He ignored the loud swish and roar of the machines as he immersed himself in chapter six, taking a swig of the cool, crisp soda. 

Sometime later, Sam was yanked from behind Holden Caufield’s eyes and slammed back into the stark fluorescent light of the EZ Wash by a loud buzz. The first machine had already finished its cycle. He stood up and jammed his hand in his pocket, fishing out the rest of his change. At this point, the industrial sized dryers were all occupied so Sam took an armful of wet clothes and wandered over to the regular ones. He found an open machine and popped the laundry in, paying the $.50 and setting the temp to high. 

The other washer finished too and Sam loaded the rest of the wet clothes across five random dryers. He snagged one of the aging chrome laundry baskets on wheels on the way back to his book and soda. He’d collect all the separate loads in the basket and fold everything over in his quiet corner before heading back to the motel. 

Sam got through another two chapters before his rumbling tummy convinced him to check on the clothes. His soda was gone and so was all his change. He pulled the cart over to the first dryer. It was still running but the clothes looked mostly dry. There was a teenage girl, around Sam’s age, maybe a bit older, unloading the machine next to his. He gave her a half smile and nod in acknowledgement as he opened the machine. 

The girl was lanky and sort of awkward, not unlike Sam. Her reddish-brown hair was up in a loose, messy bun and she wore a faded blue tank top and hand-me-down jeans that were too short for her long, lean legs. Sam’s eyes wandered carelessly over her freckled clavicle and the assortment of necklaces that trailed down into her B-cup cleavage. She wasn’t wearing a bra. 

He let his gaze linger just a moment too long as he mindlessly emptied his clothes. When finished and turned to shut the dryer door, the movement pulled Sam out of his daze and their eyes met for a horrifically awkward moment. She turned a bright shade of pink and did a quick 180, almost bumping into the woman to her right who was checking on the load in the next machine. 

“Going to the bathroom, Mom!” She chirped as she scurried away, not waiting from acknowledgement from her mother. 

Sam blushed fiercely, feeling like a complete jerk. He hadn’t meant to stare, especially not so openly. Sam wasn’t even 100% sure he liked girls – in that way – and he certainly wasn’t a pervert. Sam grabbed the lip of the rolling basket and headed back over to his duffle bag before he had the opportunity to make an even bigger ass out of himself. He decided to just fold everything later when he got back to the motel and save himself. and the poor girl, any more embarrassment. 

Sam bent over and opened the bag, reaching blindly into the basket of clean laundry for a handful to shove inside. A flash of color caught his eye and he looked down at the garments in his hand. Holy shit. These weren’t their clothes. 

Sam’s eyes widened in shock as he recognized the soft, feminine garments in his hand. Panties. Pretty, cotton ones. His hand twitched as he examined them in awe. There were two pairs; one white with assorted sizes of pale blue hearts and one vibrant teal with a white satin bow at the front. They rested in his palm, partially tangled in one another, draped around his slender fingers. He stood up, dropping the duffle bag as his mind reeled with fresh humiliation as it tried to figure out what had caused this terrible mistake. 

“Excuse me, young man? I don’t think that belongs to you…” The woman’s voice was soft and gentle but a jolt of panic ran up Sam’s spine, nonetheless. Instinct kicked in and Sam clenched his fist around the small scraps of cotton, trying to make them smaller. Then, in a flash of pure, unadulterated panic, he shoved the incriminating evidence down the front of his pants, past the sagging elastic band of his heather-grey boxer briefs. 

“Uh – yeah, oh wow, I’m – I’m so sorry! I didn’t realize!” Sam’s voice trembled and cracked as he turned around completely flustered. He felt the burn of embarrassment wash over his face, turning him beet-red for a second time. He averted his eyes, blindly shoving the rolling cart toward the petite, dark haired woman. 

“That’s okay, accidents happen. I mean, all of these carts look the same. I think that one over there is yours.” She said motioning to the cart on the opposite side of the dryer he’d just unloaded. 

In his earlier embarrassment, he’d snagged the wrong cart. A simple mistake. She probably wouldn’t have the same sentiment if he knew he had a few pairs of her little girl’s undies stowed next to his dick. Sam peeked at her from under the fringe of his bangs, smiling awkwardly and praying she hadn’t seen what he had done. She just smiled back with warmth and understanding before turning to pull her cart over to the rest of her laundry pile.

Sam swallowed the immense lump in his throat and grabbed the duffel bag, shoving the Tide and his book into the bottom. He quickly emptied each of the other dryers of their still-damp clothes before returning to the cart he’d abandoned. It was three feet away from where the girl and her mom were now sitting, quietly folding their clean clothes. Sam kept his eyes on the laundry as he shoved the remaining articles from the basket into his bag, not bothering to hide his haste. When he was done, he scurried past them, mumbling a quick apology.

“So-sorry about that, have a great night!” Sam couldn’t even look at their faces he was so mortified. The small wad of cotton tucked next to the base of his cock felt like a giant blinking sign flashing the word “PERVERT!” 

Once he was around the corner of the building, Sam ran full tilt all the way back to the motel with the heavy duffel bag in tow. His heart was pounding in his chest when he slammed the door behind him and let himself crumple against it, trying to catch his breath. He checked the peep hole a few times just to make sure no one had followed. Sam had never actually stolen anything before, much less some poor girl’s underthings. 

Once his heart stopped pounding in his ears and his lungs stopped burning, Sam chucked the duffel of laundry onto the floor next to the bed, too freaked out to worry about folding it anytime soon. The shower was on and he could hear Dean crooning some crappy power ballad over the sound of the water. 

Sam reached down the front of his pants, fishing the wad of cotton out of his boxer briefs. The fabric was warm and slightly damp from the sweat generated during his dash home. He backed up and sat on the edge of the bed as he unfurled the bundle of cloth in his hands, running his fingers over it dreamily. 

“Uh, Sam?” Suddenly Dean was there, standing in the doorway of the bathroom, with a towel tied low around his narrow waist. Sam looked up at his brother, all too aware of how deer-in-the-headlights his expression must be. Sam hadn’t even heard Dean get out of the shower. He was too lost in his own head.

“Whatcha got there, Sammy?” Dean cocked his eyebrow and grinned, looking way more pleased then necessary. Sam glanced down at the prize in his palm and back up at Dean, struggling for words to explain. Unfortunately, his teenage libido was in temporary control of his frontal lobe again. His eyes were doing that hungry, flesh devouring move they had back at the Laundromat. Only this time, Sam sat gaping at his mostly naked, shower-damp brother, and this time he was feeling a definite surge of lust.

As Sam’s mouth hung open, attempting to choke out an explanation, Dean crossed the space between them with a knowing look on his face. His hand slid up over Sam’s and tugged the white pair with blue hearts gently out of his loose grip. Dean spread them out in his hands, running his own fingers over the cotton and grinning softly as if he were recalling a fond memory. 

“There’s nothing like making a girl damp for you through her cotton panties….” Their eyes met again. Dean let the words trail off, swallowing thickly and licking his lips. Sam’s erection throbbed uncomfortably in his jeans and he tugged his baggy t-shirt down, trying to conceal the effect his brother was having. Dean’s eyes followed the movement, locking onto Sam’s crotch.

“Just kissing ‘em deep, stroking their neck, thumbing over those hard little nipples…” Dean’s voice was dreamy and thick with lust. "It's usually enough to get them soaking wet for you... If you know what you're doing..." 

Dean palmed the panties and dropped his free hand to the edge of his towel, flicking it open. It dropped to the floor between Sam’s feet with a muffled, wet thud. There was that smile again, Dean was suddenly a cartoon wolf and Sam felt like Little Red Riding Hood. 

Dean held the eye contact as he stepped into the panties, one leg at a time. Sam watched transfixed as he pulled them up over his calves and knees. The thin, stretchy material slid whisper soft over the pale golden hairs on Dean’s thighs before he paused to run his hands along the elastic, tugging them up over the curve of his ass. 

“A little snug but they’ll do.” Dean said softly as he tucked his balls and half hard cock inside. The fabric stretched to accommodate, but the weight of his sizeable package tugged the front of the panties down so a tuft of light brown hair was peeking out over the lacy edge. Sam swallowed so thickly that the gulp was audible. 

“Come on, baby boy. Your turn.” Dean yanked on the turquoise panties that Sam still had clutched tightly in his fist, pulling them free and dangling them in the air. 

“Get undressed.” Dean just held the panties expectantly, watching Sam and waiting. He ran his free hand over the white cotton that was clinging to his hip, running his fingertips down over the bulge of his cock, stroking himself patiently. 

Sam didn’t know much at the moment, his mind was swirling with adrenaline and lust, but he knew he wanted whatever Dean had to give. He grabbed the hem of his shirt again, dragging it up his torso and over his head. He fumbled nervously with his fly – too eager to undress and too busy watching Dean caressing himself through the pretty cotton. Dean chuckled softly and tossed the panties on the bed next to Sam. 

“Here.” Dean pushed Sam’s clammy fingers away from the waist of his jeans and made quick work of them, yanking them down to discard in a heap next to his towel. Dean traced his hands back up Sam’s legs, gripping his boxers at the hip and pulling them off next. Sam gasped a little and felt the flush in his cheeks spread down his chest as he was laid bare before his beautiful, tan brother. 

Sam didn’t think much of his skinny hips, still soft with baby fat, and his pale thighs that hadn’t figured out how to build long, lean muscle yet. He still felt clumsy and self-conscious in his own skin. His knees fell together in a half hearted attempt to hide his slender pink cock that was leaking like a faucet against his hairless belly. It just seemed so… pretty compared to the thick, veiny shaft that Dean stood stroking in wait. Dean’s cock was intimidating, even when it was tucked inside girly things.

“Don’t be shy, Sammy.” Dean tugged Sam’s right arm, heaving him back up onto his feet before tucking the teal panties into Sam’s other hand. Sam put them on quickly, eager for the skimpy piece of fabric to cover his sensitive boy bits. His pair fit a little better than the ones Dean wore because he was smaller and more supple, like the sweet girl these had once belonged to. His hands were almost shockingly clammy and cold on his fevered skin as he tucked his hard on under the narrow waistband. Sam plucked awkwardly at the little white bow before looking up at Dean from under his long lashes, chewing his bottom lip nervously. 

“Christ.” Dean exclaimed. He gave his now fully erect cock a firm squeeze as his olive green eyes devoured Sam’s body. Embarrassment swelled in Sam again and he tried to look away but Dean’s raised his hand, caressing Sam’s neck, over his cheek, using his thumb to tilt Sam’s chin up. 

“Look at me.” Dean slotted his body up against Sam’s as their eyes met. His thumb traced the edge of Sam’s jaw as he spoke.

“So gorgeous, Sammy. Prettier than any fuckin’ girl.” The fingers of Dean’s other hand slid between Sam’s thighs, slow and gentle. “Gonna get wet for me, babe?” 

Dean worked his way up, running his fingertips over the curve of Sam’s balls. His hand lingered there, fanning out, and the broad heat of his palm engulfed Sam’s dick through the cotton. Sam knew he was already dripping and Dean’s hand pressed the wet tip of his hard on into the fabric, causing it to grow moist and dark. Sam groaned and grabbed onto Dean’s shoulders, worried his knees would give in. He let his body slump into Dean’s for support, the pressure sandwiching Dean’s hand between their bodies, making the pressure on Sam’s cock urgent and almost unbearable. 

That’s when Dean kissed him, while Sam’s eyes were still closed and his mouth was open, panting, and wet. The kiss was slow, giving, and utterly delicious, like the taste of honey on warm bread. 

Sam kissed back desperately, sloppy and too eager, he knew it wasn’t good but Dean led him patiently, still stroking over his cheek, fingers trailing into the tendrils of hair at Sam’s neck. Sam didn’t remember even needing to breathe, his mind cleared of anything but the explosion of heat that spread through his body as Dean’s tongue licked deeper into his mouth, tasting him completely. 

Dean’s hand was firm and motionless, cupping Sam’s length as they kissed. He began moving his hand again as he pulled away. He traced his index finger up the underside of Sam’s painfully hard erection and circled the ridge of its head before dipping over the slit. Sam gasped again, chasing Dean’s mouth, as his brother attempted to pull away. 

“Get on the bed, okay?” Dean’s voice was quiet and raw as he guided Sam back onto the mattress. Sam got on the bed and shoved the scratchy floral bedspread off onto the floor as Dean went into the bathroom. There was the sound of rummaging and a zipper closing before he returned with a small, clear bottle in his hand. Sam knelt at the center of the bed with his knees splayed wide, watching Dean as he sat the bottle on the nightstand and climbed on the bed next to him. He took Sam’s mouth in another deep kiss. His hands went to Sam’s neck again, using the edge of his fingernails to trace long, dreamy lines from the nape down to the dip in his clavicle. He kissed along Sam’s jaw – plush, pillow kisses all the way to his earlobe. Dean’s hand slipped lower and caresed the smooth skin of Sam’s chest. His fingertips swirled causing goosebumps to erupt over Sam’s torso and down his arms. Sam whimpered, his nipples were diamond hard and he could feel precome soaking an even bigger stain into the cotton encasing his cock. 

“See what I mean? Already so wet for me.” Dean coaxed Sam gently onto his back. Dean followed, lying on his side next to him. They kissed again, fluid and easy, falling into a smooth rhythm of lips, tongue, and stuttered breath. Dean’s knee slid up over Sam’s thigh and his hand traveled down the curve of his waist. He tilted their pelvises together and bucked gently, rubbing the tips of their cocks through the supple cotton. 

Sam’s erection was straining, jutting out almost uncomfortably, as if it were trying to escape the small triangle of fabric. It leapt and leaked wildly as Dean’s cock grazed his for the first time. Even through the two layers of fabric, Sam could feel every vein, every ridge of Dean’s cock as it slid along his. They both groaned loudly into their kiss, hands pulling one another closer, as they began to rut against one another in earnest. 

Dean’s arms wrapped around Sam and his hands gripped the soft flesh of Sam’s ass. The undersides of their cocks rubbed together more aggressively as Dean found a rhythm, canting his hips and squeezing Sam against him. Sam let Dean guide their movements, gasping from each sharp thrust. 

“Fuck, Dean. Oh my God…” The tip of Sam’s cock was slip-sliding in the precome that drenched the front of his underwear and he whimpered each time the cotton smoothed ridges of their cockheads bumped over one another. 

“Feels so fucking good, Sam. Come on, harder. Rub against me.” His voice was almost gravely, barely hiding his trembling breath as their bodies rocked together. 

With their mouths still connected, Sam pushed Dean back and climbed on top of him. He straddled Dean’s pelvis and started grinding down. Sam savored the sight of Dean gasping and writhing as their dicks stroked through the stolen panties. He felt so powerful, so raw and filthy. He was going to come harder than he had in his entire life. 

Dean seemed equally affected by Sam’s aggressiveness. He grabbed Sam’s waist and bent his knees, bucking up into him. There was so much precome slicking the front of Sam’s panties that the tip of his cock began slipping out from beneath the waistband. He cried out when the elastic of the panties snagged right below his slit, forcing out another blurt of precome. Dean’s hand moved off Sam’s hip and he ran his thumb over the angry red tip of Sam’s cock, collecting the dewy bead of slick. Sam whimpered and watched as Dean dragged his tongue over his thumb, eyelashes fluttering as he tasted Sam’s essence. 

“Mmm, come for me, Sammy. Wanna taste you.” 

Sam watched hungrily as Dean’s tongue wet his plush, pink lips. That was all it took. Sam’s hips pumped erratically as his balls seized up and he cried out, sounding almost pained. He felt the hot splash of come against his stomach before his hips bucked, dragging the tip of his cock back under the waistband of his panties. Sam felt the backsplash of come fill the snug space as he unloaded spurt after spurt against the fabric. 

Dean gripped him brutally and his fingertips dug into the meat of Sam’s ass. His cock rutted roughly into the groove between Sam’s cock and the jut of his hip bone. It only took a few more thrusts before Dean cried out and his body seized up under Sam’s. He was coming too, all over the little blue hearts. 

A smile spread across Sam’s face as he rode out the last of the aftershocks, letting his head tilt down to rest in a sweaty smear against the front of Dean’s shoulder. Dean was breathing like he’d just run a marathon and he released his grip on Sam’s pelvis to begin smoothing his hands over the top of his thighs. 

“Made a little mess…” Dean said as he ran his fingers along Sam’s abdomen, collecting the streaks of come that had escaped before his dick slipped back into his panties. Sam watched, still panting, as Dean sucked Sam’s come off his fingertips. 

Sam leaned forward and pressed their lips together, chasing the come with his tongue. Dean groaned loudly into the kiss and his hips twitched as they pushed Sam’s seed back and forth between their mouths. Sam pulled away, hungry for more. He slipped down between Dean’s thighs, kissing and licking a trail down Dean’s torso. The taste fresh sweat and the faint smell of the motel’s cheap, complimentary soap momentarily erased the flavor of come from his taste buds. 

The front of Dean’s panties were soaked through making the thin, white cotton look almost translucent where it clung to his softening cock. Sam licked along the wet fabric, enjoying the sensation of the warm, wet cotton against the texture of his tongue. Dean whimpered and brought his hand to Sam’s shoulder, gently stroking. 

Sam traced his tongue along the ruffled elastic edge before hooking his fingers in to tug the panties down. Dean’s ass held them up in the back so Sam just tucked the edge under his brother’s balls as he began to lick again. He started with little kitten licks, lapping at the sizeable pool of come that had collected at the curve of Dean’s hip. It was slightly bitter and salty like Sam’s but there was a different, slightly earthy quality to it, something that made it very Dean. Sam wanted to devour every last drop. 

His own crotch was soaking wet and the panties were bunching uncomfortably around his sack but Sam could still feel his teenage libido tickling at the edge of his mind. His senses were flooded with Dean and he knew he would get hard again, just from the taste of his brother on his tongue. 

“Fuck, Sammy. Such a good boy, cleanin’ me up.” Dean had propped himself up on his elbows and was looking down at Sam. When their eyes met, Dean’s cock twitched under Sam’s tongue, plumping again at the sight. 

“God, you’re good at that…” Dean cooed, as Sam licked broad stripes up Dean’s slowly stiffening erection. Sam licked it clean, enjoying the sounds his brother made as his tongue traced over him. He was slow and thorough, not satisfied until Dean’s skin tasted only of his own spit. 

By the time he was done Dean was fully hard again with his legs splayed wide to accomodate Sam’s shoulders. Sam traced Dean’s cock with his tongue once more, from root to tip, before taking the head between his lips. Dean’s eyes were closed and his head tipped back when Sam engulfed him. His back arched and he clawed at the sheets at the sensation of Sam taking him in his mouth as far as he could. 

Sam groaned at the weight of Dean’s dick on his tongue, the sensation of its blunt tip pressing into his spongy soft pallet. The vibration around Dean’s cock made him whimper, hips bucking reflexively, slipping it even further into Sam’s throat. Sam’s eyes watered a bit as he wrapped his hand around the part of Dean’s cock he couldn’t take. He stabilized Dean’s hip with his other hand and gulped at the spit and precome that had flooded his mouth. He began bobbing his head up and down, going slow, finding an easy rhythm. 

“Fuck, Sammy. So good.” Dean’s hand raked through Sam’s hair. “Perfect fuckin’ mouth, so good on my cock, baby. Don’t stop.” 

Sam smiled at the praise, working Dean’s dick with his hand and mouth in unison. He could only make it about half way down Dean’s length but he could feel himself opening up, knew his throat could take it deeper if he practiced. Dean whined and quivered under him and Sam’s own dick responded, growing fully hard again in his come-slick panties. After a few minutes, Dean propped himself up and pushed gently against Sam’s shoulder, urging him to back away. 

“You keep doin’ that and I’m gonna lose it, Sam. Wanna try somethin’ else.” 

Sam let Dean’s spit-slicked cock slip out of his mouth, licking his lips and watching his brother intently. It took a moment for Dean to regain his composure after his heavy dick bobbed back against his stomach. He ran his thumb over Sam’s lower lip before climbing behind him and tugging down his panties. 

“So dirty, got your panties all wet…” Dean clucked as he pulled the undies down Sam’s thighs, leaving them bunched around his knees. Dean reached around and ran his hand over Sam’s come-covered cock, jacking it slowly as the fingers of his other hand traced up Sam’s ass crack. Dean teased over his asshole, gently stroking it with the pads of his fingers. Sam groaned and arched his back, oscillating between the two intense sensations. 

“You like that, Sammy? Want me to play with your wet little pussy?” Dean’s breath was hot against Sam’s ass cheek but his words were even hotter. He swiped his tongue playfully along the edge of Sam’s crack. Sam whimpered. He was ready and willing to take whatever Dean was planning to give him. Dean released Sam’s dick and took Sam’s hips in both hands. He rubbed his large palms over the smooth curves of Sam’s ass, pulling his cheeks apart with his thumbs. 

Dean kissed Sam’s hole softly at first, the same way he had kissed his mouth when their game began, pressing his supple lips gently against the tender skin. He soon deepened the kisses, laving his tongue over the puckered skin, tracing the opening and flickering against it again and again. 

The sensation was like nothing Sam had ever felt. Experimenting with his own slender fingers felt nothing like the pliant, wet, probing of Dean’s tongue. He could feel his body opening for Dean, wanting his tongue deeper. Sam bucked back into the heat of Dean’s mouth, needy and hungry for more. 

“Fuck yes, open up for me,” Dean panted before he plunged his tongue back in, pointing and pressing inside, just to pull away again, “fuckin’ pretty little hole.” Dean spoke almost reverently, kissing and sucking at Sam’s sensitive opening. 

“Please, Dean...” Sam whimpered, “more…” He glanced back at Dean over his shoulder. His brother looked absolutely debauched. His mouth was bright pink, his lips were almost as swollen as if he’d been punched, and his pupils were wide and eyes hungry with lust. 

Sam reached up and grabbed the small bottle of lube off of the night stand. He recognized it as the one he’d sneaked it out of Dean’s shaving kit a few times to finger himself in the shower. He couldn’t even imagine how much better it would feel with Dean’s thick digits stretching him open. 

He passed the bottle to Dean who didn’t hesitate to click open the lid and squirt some of the thin liquid onto his fingers. He spread the slick up and down over Sam’s crack liberally, dipping the tip of his finger into the pucker he’d licked open with his tongue. Sam’s hole was needy and it clenched around Dean’s teasing fingertip as he pressed back into the intrusion, letting Dean slip in to the first knuckle. 

“God, Sammy. So tight.” Dean groaned as began thrusting his finger in and out shallowly, pressing just a bit deeper each time. It didn’t sting yet. Sam was used to taking two of his own fingers regularly. He wanted Dean deeper and kept pushing his butt back. 

“Fuck, you need it bad, huh baby?” Dean groaned. Sam looked back at Dean, nodding and biting his lip. 

“Can you take two?” Dean asked, tracing his other finger around Sam’s rim. 

“Yes… God…” Sam whined, desperate and needy. 

Dean slipped his finger out and pushed forward again with both digits. Sam focused on relaxing, opening to the intrusion. It was tight but Dean’s fingers were slick. He sank them in slowly, past the second knuckle before backing up again, back and forth, working the muscle open. Sam gasped at the stretch, hips quivering as Dean twisted his fingers. 

“That’s it baby, open for me. Gotta stretch that little pussy. Get it all wet and ready for me.” Dean’s words were like fire in Sam’s veins. Fuck yes he wanted Dean to open him up, fuck into him with those long, thick fingers. He’d be a million times sweeter and tighter than those teenage pussies Dean was always chasing. God yes, Sam wanted it. He needed it. 

Dean’s fingers were doing their job making Sam’s hole wet and open. His rim was twitching around Dean’s fingers now, accepting his gentle thrusts. Sam arched his back, taking Dean’s hand all the way to his knuckles and continued pushing back, wanting more. He didn’t have to ask. 

Dean found the lube again and drizzled some of the cool liquid down Sam’s crack. It flowed around his clenching rim and the fingers that were slipping out, leaving his hole feeling empty and open. Dean wet his ring finger in the stream of lube that was trickling down Sam’s balls before returning to the opening and pressing in again. 

Three fingers burned. Sam bit his lip and pressed back against the intrusion to let Dean know he wanted it, even if it hurt a little. The burn radiated out from his opening, sending jolts of electricity up his perineum and the tip of his leaking cock. Sam bucked back on Dean’s still hand desperately, like a needy little slut.  
“Slow down, baby. Don’t want you to hurt yourself.” Dean soothed his hand up and down Sam’s sweaty back. He twisted his fingers again and curved them inside, just a bit. Sam tried to steady himself but the pleasure building within him made it hard to stay still. 

“Dean…. Pleassseeee… Harder…” He was whimpering desperately as Dean’s fingers grazed his prostate. He’d never been able to find it on his own but Dean’s fingertips flicked against it expertly as they undulated inside him. 

By then Dean was thrusting in a solid rhythm and Sam had loosened around him quickly in his arousal. His lubed up fingers slid in and out with almost no resistance. Sam’s cock was dripping almost constantly and his body felt like one giant, raw nerve, like he was coming apart at the seams. It was so good. Sam never wanted it to end. 

“That better? So wet for me, Sam. Such a pretty pussy.” Dean’s voice was strained, his words faded at the end. “God, I want to fuck you...”

Sam panted and lifted his head with some effort, looking over his shoulder again at his brother. 

“Yes, please. I need it so bad, Dean…” Sam’s mouth was dry from exertion but he licked his lips, grinning hopefully. “Need you to fuck my wet pussy.” The words made Sam’s dick twitch. He was so close to coming but he wanted to feel Dean split him open on his fat dick before he did. 

“Need you in me, want you in me when I come.” Sam begged. Dean’s eyes slammed shut and he grabbed the base of his erection, squeezing tightly with his other hand. 

“Fuck, Sam. Can’t talk like that anymore or I’m not gonna last.” Dean chuckled, his knuckles were almost white as he strangled the base of his dick. Sam smiled and pushed his butt back into Dean’s hand again. Dean flicked his fingers deep inside Sam, flicking his prostate before slowly pulling his hand free. 

“Flip over, wanna watch you…” Dean pressed against Sam’s flank, nudging him to get on his back. Dean sat back on his haunches and found the lube again. Sam turned over and finally pulled the ruined panties off, chucking them onto the floor, forgotten. He opened his legs on either side of his brother, sliding his butt down to bump against Dean’s knees. Dean’s lube coated hand slipped over his own erection before he moved it between Sam’s legs and swiped the remaining slick over Sam’s fluttering hole. 

Dean’s cock bobbed heavily, stiff and shiny, between Sam’s thighs. He slid his thumb along the top of his cock, pressing the tip downward as he leaned forward over Sam. The head felt so incredibly wide when Dean finally pressed it against Sam’s opening. Sam gasped and gripped Dean’s hips, slowing him. He was rocking his hips minutely, letting Sam’s hole get used to the hot, blunt pressure. The lube helped Sam’s pliant rim open and accept it a little deeper each time. He held it there with firm, even pressure, moving in and out ever so slightly. 

Sam’s erection had started to flag a bit in apprehension of the pain. Dean palmed it, curling his warm, still-slick hand around Sam’s cock, and jacked it slowly back to full firmness. Sam breathed deep and tried to relax. He wanted nothing more than for Dean to be inside him with the head of that thick, veiny dick fucking deep into his stomach. He focused on opening and relaxing into the pressure. 

“Push, Sam.” Dean’s voice was nearly a whisper and Sam knew exactly what he meant. Dean’s hips pressed forward a bit more and Sam bore down against the intrusion. His rim finally relented, stinging as it opened wide to accept the entire head. The flared edge popping past Sam’s rim was like a bright burst of flame. Sam cried out and arched his back from the blast of pain. Dean pressed onward and Sam’s hole relented. He slid in smoothly, only stopping when his hips were pressed against Sam’s. 

Sam saw stars as the head rocked against his prostate. Waves of pleasure washed over him, erasing the ache. As the pain relented, Sam could feel his hole throbbing with heat around Dean’s shaft. It fluttered eagerly, begging for movement. Dean was so still, his breath was hot and staggered next to Sam’s face. He was completely on top of and inside of Sam.

“You okay, baby?” Dean asked softly. Sam whimpered and nodded quickly. It was all he could muster as he willed the rest of his body to relax and accept his brother’s gift. Dean kissed the side of his face, moving down to his neck where he began nibbling and licking to distract Sam for the first drag of that big, thick cock inside him. 

Dean kept his thrusts deep but shallow at first, letting Sam’s insides get used to a gentle rhythm. The pressure was incredible, and Sam really did feel impaled, but the warmth and comfort of Dean wrapped around him made it easier to relax into the mix of sensations. Sam whimpered with each thrust. Short little yips of discomfort quickly melting into breathy, mewls of pleasure. 

“That’s it baby. Feeling better? Does your little pussy like that, Sammy?” Dean slurred in Sam’s ear, drunk on lust. He rocked back on his knees to get his arm hooked under Sam’s right knee, pushing forward again with Sam’s hips tilted up, legs open wide. The angle made Dean’s dick slam directly into Sam’s sweet spot. It only took a few deep, slick thrusts before Sam was emptying his balls for a second time, all over Dean’s stomach. 

“Shit, Sammy. So fucking good, so tight –“Dean’s own words seemed to tip him over the edge, immediately after Sam. He came, buried deep inside. Pulse after pulse of come emptied into Sam as Dean’s hips stuttered and twitched against him. 

They lay there entangled, bodies sweaty and twitching, slotted together and connected. Sam basked in the waves of pleasure that continued to wash over him for what seemed like long, blissful hours. Eventually, he tilted his face toward Dean’s and practically open mouth kissed his sweaty cheekbone, panting against Dean’s salty, slightly stubbled face. Sam wanted to feel this full, loved, and complete always. 

Dean pushed himself up off of Sam a bit, moving hips to let his softening cock slip dirty-wet out of Sam’s body. Sam’s hole shuddered, so empty, open and slick, missing Dean already. Dean smiled and kissed him softly, punctuated with a shallow lick into Sam’s mouth, sucking gently on his bottom lip. 

“We need to talk,” Dean said as his lips still hovered over Sam’s, “about when my little brother became a fuckin’ panty thief.”

**Works inspired by this one:**

  * [The Panty Thief (Podfic)](https://archiveofourown.org/works/1453837) by [Oddfront](https://archiveofourown.org/users/Oddfront/pseuds/Oddfront)




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